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CAS Number: 117-84-0
EC Number: 271-085-1
Molecular formula: C24H38O4
Molar mass: 390.56 g
IUPAC name: 1,2-dioctyl benzene-1,2-dicarboxylate
Dioctyl phthalate (often imprecise dioctyl phthalate) is an organic chemical compound from the group of phthalates ( esters of phthalic acid ), which is mainly used as a plasticizer .
Dioctyl phthalate is a colorless, odorless, oily liquid and a structural isomer of diethylhexyl phthalate (Dioctyl phthalate).
Dioctyl phthalate Extraction and representation
Dioctyl phthalate is obtained by reacting phthalic anhydride with octanol in the presence of a catalyst.
Dioctyl phthalate Properties
Dioctyl phthalate is a colorless odorless liquid which is practically insoluble in water.
Dioctyl phthalate Usage
Dioctyl phthalate is used as a plasticizer (e.g. for PVC), a component of anti-foaming agents , solvents and as a varnish resin and is therefore used for applications in the cosmetics industry, in the medical sector and in the explosives industry.
Dioctyl phthalate is also used in the production of test aerosols.
Dioctyl phthalate appears as a clear liquid with a mild odor. Slightly less dense than water and insoluble in water.
Hence floats on water. Flash point 430°F. The primary hazard is the threat to the environment.
Immediate steps should be taken to limit its spread to the environment.
Dioctyl phthalate as a liquid, can easily penetrate the soil and contaminate groundwater and nearby streams.
Eye contact may produce severe irritation and direct skin contact may produce mild irritation.
Dioctyl phthalate is used in the manufacture of a variety of plastics and coating products.
Dioctyl phthalate is a colorless, odorless, oily liquid that doesn't evaporate easily.
Dioctyl phthalate is a man-made substance used to keep plastics soft or more flexible.
Dioctyl phthalate can be used for medical tubing and blood storage bags, wire and cables, carpetback coating, floor tile, and adhesives.
Dioctyl phthalate is also used in cosmetics and pesticides.
Dioctyl phthalate is a phthalate ester and a diester.
Physical state: fluid
density: 0.98 g/cm
Melting point: −49 ° C
Boiling point: 385 ° C
Vapor pressure: 1 Pa (20 ° C)
Solubility: Practically insoluble in water
XLogP3: 9.1
Hydrogen Bond Donor Count : 0
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 18
Exact Mass: 390.27700969
Monoisotopic Mass: 390.27700969
Topological Polar Surface Area: 52.6 Ų
Heavy Atom Count: 28
Formal Charge: 0
Complexity: 369
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Dioctyl phthalate Physical Descriptions
Dioctyl phthalate appears as a clear liquid with a mild odor. Slightly less dense than water and insoluble in water.
Hence floats on water.
Flash point 430°F.
The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment.
As a liquid, can easily penetrate the soil and contaminate groundwater and nearby streams.
Eye contact may produce severe irritation and direct skin contact may produce mild irritation.
Dioctyl phthalate is used in the manufacture of a variety of plastics and coating products.
Due to Dioctyl phthalates suitable properties and the low cost, Dioctyl phthalate is widely used as a plasticizer in manufacturing of articles made of PVC.
Plastics may contain 1% to 40% of Dioctyl phthalate.
Dioctyl phthalate is also used as a hydraulic fluid and as a dielectric fluid in capacitors. Dioctyl phthalate also finds use as a solvent in glowsticks.
Approximately three billion kilograms are produced and used annually worldwide.
Manufacturers of flexible PVC articles can choose among several alternative plasticizers offering similar technical properties as Dioctyl phthalate.
These alternatives include other phthalates such as diisononyl phthalate (DINP), di-2-propyl heptyl phthalate (DPHP), diisodecyl phthalate (DIDP), and non-phthalates such as 1,2-cyclohexane dicarboxylic acid diisononyl ester (DINCH), dioctyl terephthalate (DOTP), and citrate esters.
Environmental exposure
Dioctyl phthalate is a component of many household items, including tablecloths, floor tiles, shower curtains, garden hoses, rainwear, dolls, toys, shoes, medical tubing, furniture upholstery, and swimming pool liners.
Dioctyl phthalate is an indoor air pollutant in homes and schools.
Common exposures come from the use of Dioctyl phthalate as a fragrance carrier in cosmetics, personal care products, laundry detergents, colognes, scented candles, and air fresheners.
The most common exposure to Dioctyl phthalate comes through food with an average consumption of 0.25 milligrams per day.
Dioctyl phthalate can also leach into a liquid that comes in contact with the plastic; it extracts faster into nonpolar solvents (e.g. oils and fats in foods packed in PVC).
Fatty foods that are packaged in plastics that contain Dioctyl phthalate are more likely to have higher concentrations such as milk products, fish or seafood, and oils.
Food and Drug Administration (FDA) therefore permits use of Dioctyl phthalate-containing packaging only for foods that primarily contain water.
Dioctyl phthalatecan leach into drinking water from discharges from rubber and chemical factories; The US EPA limits for Dioctyl phthalate in drinking water is 6 ppb.
Dioctyl phthalate is also commonly found in bottled water, but unlike tap water, the EPA does not regulate levels in bottled water.
Dioctyl phthalate levels in some European samples of milk, were found at 2000 times higher than the EPA Safe Drinking Water limits (12,000 ppb).
Levels of Dioctyl phthalate in some European cheeses and creams were even higher, up to 200,000 ppb, in 1994.
Additionally, workers in factories that utilize Dioctyl phthalate in production experience greater exposure.
The U.S. agency OSHA's limit for occupational exposure is 5 mg/m3 of air.
Use in medical devices
Dioctyl phthalate is the most common phthalate plasticizer in medical devices such as intravenous tubing and bags, IV catheters, nasogastric tubes, dialysis bags and tubing, blood bags and transfusion tubing, and air tubes.
Dioctyl phthalate makes these plastics softer and more flexible and was first introduced in the 1940s in blood bags.
For this reason, concern has been expressed about leachates of Dioctyl phthalate transported into the patient, especially for those requiring extensive infusions or those who are at the highest risk of developmental abnormalities, e.g. newborns in intensive care nursery settings, hemophiliacs, kidney dialysis patients, neonates, premature babies, lactating, and pregnant women.
According to the European Commission Scientific Committee on Health and Environmental Risks (SCHER), exposure to Dioctyl phthalate may exceed the tolerable daily intake in some specific population groups, namely people exposed through medical procedures such as kidney dialysis.
A review article in 2010 in the Journal of Transfusion Medicine showed a consensus that the benefits of a lifesaving treatments with these devices far outweigh the risks of Dioctyl phthalateleaching out of these devices.
Although more research is needed to develop alternatives toDioctyl phthalate that gives the same benefits of being soft and flexible which are required for most medical procedures.
If a procedure requires one of these devices and if patient is at high risk to suffer from Dioctyl phthalate then aDioctyl phthalate alternative should be considered if medically safe.
Metabolism
Dioctyl phthalate hydrolyzes to mono-ethylhexyl phthalate (MEHP) and subsequently to phthalate salts. The released alcohol is susceptible to oxidation to the aldehyde and carboxylic acid.
Development
Numerous studies of Dioctyl phthalate have shown changes in sexual function and development in mice and rats.
Dioctyl phthalate exposure during pregnancy has been shown to disrupt placental growth and development in mice, resulting in higher rates of low birthweight, premature birth, and fetal loss.
In a separate study, exposure of neonatal mice to Dioctyl phthalate through lactation caused hypertrophy of the adrenal glands and higher levels of anxiety during puberty.
In another study, pubertal administration of higher-dose Dioctyl phthalate delayed puberty in rats, reduced testosterone production, and inhibited androgen-dependent development; low doses showed no effect.
APPLICATION
Dioctyl Phthalate (DOP) is a plasticizer used in the production of flexible polyvinyl chloride (PVC) plastic.
Dioctyl Phthalate is one of the most widely used plasticizers in PVC due to its low cost.
DOP is a general-purpose plasticizer and long-time industry standard known for Dioctyl phthalates good stability to heat and ultraviolet light, and broad range of compatibility for use with PVC resins.
Dioctyl Phthalate can also be used as dielectric and hydraulic fluids.
DOP is also a solvent for many chemicals, such as in glowsticks.
A light-color liquid commonly called bis(2-ethylhexyl)phthalate.
Dioctyl phthalate is used as a Plasticizer in Cellulose acetate, Cellulose acetate butyrate, Polystyrene, Vinyl chloride, and vinyl chloride acetate polymers.
Polymers may contain DOP in concentrations of 1-40%.
The European Commission has banned the use of many phthalates, including DOP, in PVC toys.
Dioctyl phthalate PROPERTIES
Dioctyl phthalate (DOP, Dioctyl phthalate), is clear, colourless, viscous liquid with a slight, characteristic odor.
Soluble in ethanol, ether, mineral oil and the majority of organic solvents.
Immiscible with water, resistant to hydrolysis and air oxygen activity.
Dioctyl phthalates high plasticizing efficiency, fusion rate, visosity, low volatility, UV-resisting property, water-extracting proof, cold-resisting property, and also good softness and electric property found a lot of applications in many offshoots of the industry.
Dioctyl phthalate APPLICATIONS
PLASTIC INDUSTRY
PLASTICIZERS
Dioctyl phthalate can be used as a softening agent , such as to make the product easier to rebound and harder to undergo form change under pressure, without affecting of the plastics.
DOP possesses its good plasticizing properties thanks to the ability to make the long polimers molecules to slide against one another.
Dioctyl phthalate is extensively used in processing polyvinyl choride and ethylcellulose resins to produce plastic film, imitation leather, electric wire, cable wearer, sheet, planet, mould plastic products and used in nitrocellulose paints.
Dioctyl phthalate has the applications in the industry of automotive, building and construction material, flooring, medical device.
WOOD COATING
Dioctyl phthalate is used in the industrial wood coating to enhance the performance properties of the wood coatings formulations.
MEDICAL DEVICES
Dioctyl phthalate is used a plasticiser in the manufacture of medical and sanitary products, such as blood bags and dialysis equipment.
Dioctyl phthalate has a further and unique role in blood bags because Dioctyl phthalate actually helps to prolong the life of the blood itself.
Dioctyl phthalate also stabilises the membranes of red blood cells enabling blood product storage in PVC blood bags for several weeks.
Product Description
DOP is still widely used as a plasticizer in selected applications where volatiles are less of an issue.
Dioctyl phthalate is also used as a hydraulic fluid and as a dielectric fluid in capacitors.
DOP was the most widely used material as a plasticizer in manufacturing of articles made of PVC.
Due to toxicity reasons, its usage has dropped and has been replaced by lower volatile phthalate and phthalate free products in some PVC and other applications.
Dioctyl phthalate, also known as dioctyl 1,2-benzenedicarboxylate or dehp, is a member of the class of compounds known as benzoic acid esters.
Benzoic acid esters are ester derivatives of benzoic acid.
Dioctyl phthalate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).
Dioctyl phthalate can be found in kohlrabi, which makes di(n-octyl) phthalate a potential biomarker for the consumption of this food product.
Dioctyl phthalate is a non-carcinogenic (not listed by IARC) potentially toxic compound.
Phthalate esters are endocrine disruptors.
Animal studies have shown that they disrupt reproductive development and can cause a number of malformations in affected young, such as reduced anogenital distance (AGD), cryptorchidism, hypospadias, and reduced fertility.
The combination of effects associated with phthalates is called 'phthalate syndrome’ (A2883) (T3DB).
Dioctyl phthalate (DOP, Dioctyl phthalate) is a diester of phthalic acid.
Dioctyl Phthalate (DOP) is a low cost, general use plasticizer, which can be useful in hydraulic fluid applications and as a dielectric fluid in capacitors.
Synomys:
1,2-Benzenedicarboxylic acid, 1,2-dioctyl ester
Phthalic acid, dioctyl ester
1,2-Benzenedicarboxylic acid, dioctyl ester
Dioctyl phthalate
Dinopol NOP
n-Octyl phthalate
Vinycizer 85
Octyl phthalate
Phthalic acid dioctyl ester
DNOP
Dioctyl o-phthalate
Dicaprylyl phthalate
NSC 15318
Bis(n-octyl) phthalate
Monocizer W 555
1,2-Dioctyl phthalate
Dioctyl phthalat
Dioctyl phthalate
DI-N-OCTYL PHTHALATE
117-84-0
dioctyl benzene-1,2-dicarboxylate
Dinopol NOP
n-Octyl phthalate
Vinicizer 85
DNOP
Phthalic acid, dioctyl ester
Polycizer 162
Phthalic acid di-n-octyl ester
Dioctyl 1,2-benzenedicarboxylate
Dioctyl o-benzenedicarboxylate
1,2-Benzenedicarboxylic acid, 1,2-dioctyl ester
RCRA waste number U107
1,2-Benzenedicarboxylic acid, dioctyl ester
Bis(n-octyl) phthalate
Dioktylester kyseliny ftalove
NSC 15318
UNII-8X3RJ0527W
1,2-Benzenedicarbonic acid, dioctyl ester
CHEBI:34679
8X3RJ0527W
MFCD00015292
68515-43-5
NCGC00090781-02
DSSTox_CID_1956
DSSTox_RID_76425
DSSTox_GSID_21956
8031-29-6
octyl 2-(octyloxycarbonyl)benzoate
di-octyl phthalate
CAS-117-84-0
Dioctyl phthalate, analytical standard
CCRIS 6196
HSDB 1345
AI3-15071 (USDA)
EINECS 204-214-7
Dioktylester kyseliny ftalove [Czech]
RCRA waste no. U107
BRN 1915994
Benzenedicarboxylic acid di-n-octyl ester
1, dioctyl ester
Vinycizer 85
di-n-octylphthalate
Dioctyl o-phthalate
Phthalic acid dioctyl
ACMC-1CJ59
SCHEMBL23053
BIDD:ER0319
CHEMBL1409747
DTXSID1021956
Phthalic acid, bis-n-octyl ester
NSC15318
ZINC8437697
Tox21_111020
Tox21_202233
Tox21_300549
0014AD
ANW-17052
Dioctyl phthalate, p.a., 99%
NSC-15318
SBB008723
STL280370
AKOS015889916
MCULE-5138747558
1,2-dioctyl benzene-1,2-dicarboxylate
NCGC00090781-01
NCGC00090781-03
NCGC00090781-04
NCGC00090781-05
NCGC00254360-01
NCGC00259782-01
Dioctyl phthalate, >=98.0% (GC)
LS-15074
benzene-1,2-dicarboxylic acid dioctyl ester
FT-0655747
FT-0667608
P0304
ST50826905
C14227
1,2-BENZENEDICARBOXYLIC ACID DIOCTYL ESTER
A803836
Q908490
J-003672
J-520376
F0001-0293
Z1235963359
Dioctyl phthalate, certified reference material, TraceCERT(R)
